The invention is a process for the preparation of .alpha.-unsaturated carboxylic esters and amides. More specifically, the process is the carbonylation of a 1,2-dihaloalkane in the presence of an alcohol or amide to prepare an .alpha.-unsaturated carboxylic ester or amide.
.alpha.-Unsaturated carboxylic esters and amides have been prepared by the carbonylation of olefinic halides. See Heck, U.S. Pat. No. 3,988,358 (incorporated herein by reference), Scheben et al., U.S. Pat. No. 3,626,005 (incorporated herein by reference), and Closson, U.S. Pat. No. 3,457,299 (incorporated herein by reference).
Methyl halides represented by the formula CX.sub.n H.sub.4-n wherein X is a halogen and n is an integer from 2 to 4 have been successfully carbonylated. See Mador et al., U.S. Pat. No. 3,454,632 (incorporated herein by reference).
Heck, Advances in Catalysis, 26, 323 at 327 (1977), teaches that saturated aliphatic halides cannot be carbonylated in the presence of palladium or nickel catalysts.
Surprisingly, saturated 1,2-dihaloalkanes have been found to undergo carbonylation under certain reaction conditions producing an .alpha.-unsaturated carboxylic ester or amide.